Base-catalyzed bis-sulfenylation of γ-substituted butenolides for the synthesis of α,α-bisthiofunctionalized butenolide derivatives

A method for the synthesis of α,α-bisthiofunctionalized butenolide compounds has been successfully developed. The bis-sulfenylation of γ-substituted butenolides at α-position is promoted by using triethylamine as the catalyst and N-(aryl(alkyl)sulfanyl)succinimides or N-(phenylsulfanyl)phthalimides...

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Bibliographic Details
Published inTetrahedron Vol. 73; no. 36; pp. 5444 - 5450
Main Authors Zhao, Jian-Qiang, Luo, Shu-Wen, Zhang, Xiao-Mei, Xu, Xiao-Ying, Zhou, Ming-Qiang, Yuan, Wei-Cheng
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 07.09.2017
Elsevier
Subjects
Bis-sulfenyaltion
Butenolides
Chemistry
Chemistry, Organic
N-(aryl(alky)sulfanyl)succinides
N-(phenylsulfanyl)phthalimides
Physical Sciences
Science & Technology
α-sulfenylated butenolides
α-sulfenylated butenolides
Bis-sulfenyaltion
Butenolides
N-(aryl(alky)sulfanyl)succinides
N-(phenylsulfanyl)phthalimides
THIOLATION
VINYLOGOUS MICHAEL ADDITION
ALKYNES
alpha-sulfenylated butenolides
C-H BONDS
BUTYROLACTONES
KETONES
S BOND FORMATION
TRIFLUOROMETHYLTHIOLATION
SULFONYL HYDRAZIDES
ALPHA-SULFENYLATION
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Summary:A method for the synthesis of α,α-bisthiofunctionalized butenolide compounds has been successfully developed. The bis-sulfenylation of γ-substituted butenolides at α-position is promoted by using triethylamine as the catalyst and N-(aryl(alkyl)sulfanyl)succinimides or N-(phenylsulfanyl)phthalimides as sulfenylating reagents under mild reaction conditions. A range of α-sulfenylated butenolide derivatives could be smoothly obtained in moderate to excellent yields. A preliminary attempt at the catalytic asymmetric α-sulfenylation of α-methyl-γ-phenyl-substituted butenolide was also conducted and afforded promising enantioselectivity. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2017.07.053